But having an easy win will be a good feeling, too, and may be helpful on the psychological side of things more than anything else.Would love to hear the thoughts of those who have a few under their belt and have had to wrestle with the variation of opportunity types.Thanks for any thoughts!

Most have a LLC for the psychological sense of protection they think it provides.

(Engineer, Doctor, Scientist, Dentist, Lawyer, Chemist, Nurse - sure then you need a degree) but if it's MBA, Psychology, Art, Music, Philosophy, etc - forgetta about it.

@Yash MirchandaniNot an expert in Wholesaling, but the aspect of seller psychology (not so much negotiation even), but just working the conversation to make the seller reveal their deeper desires and what they want to hear said to sell the property to you.

So what I am getting at is the answer to your question is half based on psychology and preference (qualitative) and just doing the number crunching analysis (quantitative).                  

I think this strategy may be more common with seller-financed deals (“your price, my terms”, or “my price, your terms”).In addition, when you give the seller several buy options, psychologically they’re more likely to compare your offers and like one more than another, rather than stepping back and evaluating whether or not any of your offers are good.

I’m a student of an area in psychology called Neuro-Linguistic Programming.

That being said, for most people, there are definitely psychological benefits to having no mortgage payment on your primary residence, especially if you are close to entering retirement.  

Motivational speakers are different, still the psychology is the same, the fearful and lazy might be better served seeing a shrink.  

After all, life is 80% psychology and 20% mechanics...